M. Palucki et al., LOW-TEMPERATURE ASYMMETRIC EPOXIDATION OF UNFUNCTIONALIZED OLEFINS CATALYZED BY (SALEN)MN(III) COMPLEXES, Tetrahedron letters, 36(31), 1995, pp. 5457-5460
The enantioselective epoxidation of olefins catalyzed by (salen)Mn(III
) complexes can be effected under anhydrous conditions with a variety
of primary oxidant systems. The combination of m-CPBA and NMO is parti
cularly reactive, allowing for epoxidation reactions to be carried out
at -78 degrees C. Under these low temperature conditions, a variety o
f unfunctionalized olefins undergo epoxidation with a significant incr
ease in enantioselectivity relative to reaction using aqueous bleach.